The Bdsm Files #2

I'm assuming if you're reading this, you've read part 1 to get the gist of where I was at...

After Maggie passed, it took me a good spell to get my head back in the right place. A number of women served as a distraction over this period of course, but it wasn't until I started to get my focus right that I came across Mistress J.

Now it may surprise you that, for me at least, I love a bossy bitchy demanding woman in the bedroom. If a woman doesn't have the nerve to kick me in the nuts or squirt right in my face...well, let's just say it won't work between us?

Somewhere along the way I ended up researching D/s relationships, for that is the closest label one could apply to what Maggie and I had. So picture me sitting in my local library in the special books section, reading up on the finer points of D/s interaction. Being a shiftworker I'd often be in the library during the morning and when I put a particular book on my waiting list I first encountered Mistress J. Who would think that an outwardly demure lady would harbour such a dark side? But I'm getting ahead of myself...

Over the course of a few weeks, it became obvious that Ms Everard was not intimidated by the subject matter I was reading up on. Looking back it was all quite subtle, her innocent questions and suggestions. Nowadays it would be called grooming no doubt, for she was assessing me as her next subject, but at the time I was a little slow on the uptake.

By the time she asked me out to lunch I caught up quick though! Helter skelter is what came next. We met for lunch at 12 sharp, and in a no nonsense manner Ms Everard questioned me. By 12.30 she had me calling her Mistress J and by 1 pm I was naked in her play room. No mental connection at first, this was pure physical fun. I needed a woman to use and abuse me, and Mistress J was quite capable of providing this for me! Down on all fours and restrained, I can still hear her sinister little laugh as she enveloped her thumb and forefinger around the base of my sack, clenches up tight and then slaps my trapped nuts with her other hand. Not once or twice, but literally until I'm crying and begging her to stop.

In hindsight it all should have been obvious. She'd been quietly observing me at the library, and her confident manner bordering on arrogant now shone thru!!

That afternoon she milked my cock numerous times, carefully catching my spunk in a wine glass each time. Watching her squeeze every last drop into the wine glass I was surprised how much cum she'd elicited from my tenderised nuts.

The focus that first afternoon was purely on hurting my nuts, seeing how much I could take, and how much cum I could produce under duress. By the time she unshackled me, my nutsack was swollen to at least twice its original size and extremely tender...but in a delicious way. To this day I love walking around with sore balls, regardless of whether this is from kicking, squeezing, slapping, punching or just merely fucking hard for hours.

Over the course of a few weeks, Mistress J, an early forties slender and tall brunette, put me thru my paces. Testing the limits of my pain, seeing what I was up for and basically seeing if I was worthy of her time.

Once she was happy that I was an ok subject to train, she really let rip on me. On my days off, she'd invariably have me come over at first light, shower and then assume the ballbusting position she preferred...on all fours in her living room. Rarely would she bother getting dressed, merely donning one of her many high heels and kicking my nutsack until I was crying. Time and again she'd order me back onto all fours, until she was satisfied the swelling was sufficient.

"Now come and fuck me!" she'd bark at me. In her bedroom, she'd just kick off her heels and lay back, legs spread and waiting for me to drag my sore nuts into position.

I soon learned that anything less than an hour of non-stop fucking Mistress J was simply unacceptable. And unacceptable in her lingo meant no orgasms for me for at least a week, watching her getting fucked by another slave, no eating pussy for at least a week, only being allowed to make her cum using my fingers...which I wasn't allowed to lick clean! Oh, and need I mention it would also include a daily ballbashing of epic proportions for the week?

So the threat here was very real, fail to please Mistress J and not only would my pleasure be withdrawn but the pain dished out would be real.

But hey, I'd learned how to fuck a woman hard for long spells, thru numerous orgasms for her of course and keeping my own back.

In time the bar would be raised higher, requiring longer spells of orgasm providing fucking. When we reached the point where I was fucking her doggy style whilst she'd smack my nuts with a wooden spoon while I was banging her...I was being severely tested!

The mental aspect had grown of course, the sole focus of my attention was to be her pussy and her orgasms. Anytime I failed to lick her just right I'd be punished in some way. Over time the eating out of my creampies was just par for the course. What I wasn't expecting was after being expected to make her cum numerous times and not cum myself, that she'd now change tack and expect me to cum inside her at short intervals. The very first time was near the airport in Auckland. Just after sundown on a summers' day, she's wearing only a pair of heels and a strappy dress, her always juicy pussy is bare beneath this dress and I know it! The rest area on the exit road is where she makes me stop, the observation tower we climbed and at the top of the tower she poses her first challenge.

"You have to cum inside me before that lady makes it to the top of the tower," she casually remarked as she nudged her head at a woman approaching the observation tower. Seeing as how it would take less than two minutes for this I wasted no time at all, she bent over and I quickly and frantically fucked her...duly emptying my nuts inside her before the lady ascending the stairs made it onto the platform. What I wasn't expecting was that Mistress J nodded at the lady as she stepped onto the platform, mind you I wasn't expecting this lady to then kick me square in the nuts either!

"Did he do good J?" the lady asked. Mistress J just nodded as she then watched the newcomer reach into my shorts, grasp my nutsack below the cock and wrap the infamous thumb and forefinger around them, thus clenching them up tight in the palm of her hand.

"How much can he handle J?" the lady asked as she's clenching me ever tighter.

For me, the mental anguish of having my nuts crushed by a woman I've not met before, nor whose name I know, with the permission of my Mistress...sheer hell and bliss at the same time.

"Who cares, just crush his balls!" J calmly stated. With this, she comes and stands alongside me, dips a finger in her pussy and scoops out a few pearls of my spunk and rubs it onto my lips.

In maybe thirty seconds I've cum inside Mistress, am getting my nuts crushed and now tears start to roll down my cheek.

"Yum, tears!" the newcomer chuckles, and with that she releases her grip.

Now I've had a few surprises in my life, but this was a new one by me. Mind you, the rest of that night was one big surprise, for the two ladies took turns tormenting me, hurting my ballbag like never before, raping my arse with a strap-on, making me eat them out for hours on end, and most of all both took turns pissing on me. The copious amounts of water they were drinking once we got home made it obvious they had some watersports planned!

Mistress J also introduced me to the party scene, albeit the private party kind. The location varied, but the same group of women would be present, a total of six mature ladies would take turns tormenting me. There was variation in the acts, but invariably they all loved smacking a guy in the nuts, raping his arse and having their pussies licked. A couple of them loved sucking cock, especially the long fused kind of cock that they could suck on fiercely...and not have to worry about it popping off early!

Now let me be upfront about this stage of my life. I both hated and loved being used like this...the intense stimulation leading up to a series of my own orgasms was addictive. Yet, the low that followed a series of orgasms was bordering on the depressive. So being the subject of attention for a group of women is great, but it ultimately is unfulfilling.

Mind you, I was getting sooooo much pussy from Mistress J that I was a long way from turning my back on this way of life. Now J had no issue sharing me around as a punching bag, or more accurately a ballbag for women to kick, but when it came to my cock going anyone...it was just for her pussy. I found this out during a party where one of the ladies took the liberty of guiding my cock into her dripping snatch whilst I was blindfolded and tied to a chair. Not only did the lady in question get turfed out, I was set upon by Mistress J in such a ferocious manner that were it not for her friends pulling me back, my nuts would not have survived...

Mistress J was intensely apologetic after this episode, and in a way things were never the same after this point. She'd lost her confidence I guess, and it wasn't until some years later that I worked out she just didn't have enough left to challenge and control me...

Mind you, the one final act that made me turn away from her was one of betrayal. Now I'm not into blood or faeces, she knew that from the get-go. Soooo, she'd been talking for a few months about nailing my ballbag to a piece of wood. In itself no big deal, she'd been instructed by another Mistress on how to, and she'd obtained a special headless stainless steel nail. Bit like a panel pin, almost no head at all and surgical stainless steel meant no risk of infection. Anyway, she'd talked about this intended act a few times but I wasn't into it, and had suggested that if she was gonna do this...to do it with one of her other slaves...

So a few months since she's last talked about this act, I find myself blindfolded, hands cuffed behind my back, ankles cuffed and made to kneel on her lawn. The group of ladies was small this time, only four in total and yet the collectively gasp alarmed me. The wooden peg that I found myself kneeling against made me think in alarm only on account of the gasp from the ladies. Feeling my nutsack being spread across the top of the peg...I knew instinctively what was next...and yes, the sharp nail went thru my sack the first time, the tap tap tap from the hammer merely followed by gasps from the ladies.

Funnily enough the pain was mild. The blindfold came off, then the shackles at my ankles.

"If you want to free yourself, the only way I will allow it is for you to stand up and yank the nail thru your useless ballbag slave!" Mistress J snarled. The gasps that followed this statement went right to my core. My stomach churned as I watched Mistress J grin at me. She meant business alright. For almost two years she's been using me, and in an effort to regain her failing grip on me, she breaks my trust by going over a hard boundary in a public manner...

Well I stood up in one swift motion, tore the nail thru my sac and ripped a vein in the process. The bleeding was profuse, albeit brief, for one of the ladies took care of me. The scar is still visible to this day, not that anyone would know of course, but I know!

Never went back to Mistress J after this, and while the lady who rescued me on that fateful day was a fun to play with for a spell...she was simply too timid on her own.

The overall mental escalation that took place over my time with Mistress J had little or nothing at all to do with love and affection. Pure lust, driven by my ability and desire to take her abuse. Ultimately this lust burned out when she couldn't keep escalating it in the right manner. Now I don't hold anything against J for breaking my trust, it was her last attempt at asserting her grip on me, and on some guys it may have worked...but my evolution was simply taking a different path to hers, not to mention I had more learning to do than J. In the end I like to think I was a joyous plaything for her, as she certainly kept me entertained for a good spell.

If I did learn anything in this time though, it was that lust on its own simply isn't enough to keep something going. There needs to be a magic combination of emotional attachment and physical naughtiness to take true steps on ones evolution.

I'll leave that for part 3